Methanol → HCID 71270835, compound

HRID 510436Notes

Reaction equation

[CH3:1]C(OC(/N=N/C(OC(C)C)=O)=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO.[Cl:36][C:37]1[C:60]([Cl:61])=[CH:59][CH:58]=[CH:57][C:38]=1[CH2:39][C:40]1[C:41]([OH:56])=[N:42][NH:43][C:44]=1[N:45]1[C:53](=[O:54])[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:46]1=[O:55]>C1COCC1.C(Cl)Cl>[Cl:36][C:37]1[C:60]([Cl:61])=[CH:59][CH:58]=[CH:57][C:38]=1[CH2:39][C:40]1[C:41]([O:56][CH3:1])=[N:42][NH:43][C:44]=1[N:45]1[C:46](=[O:55])[C:47]2[C:52](=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:53]1=[O:54]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of DIAD (1.14 g, 5.67 mmol), PPh3 (1.49 g, 5.67 mmol) and methanol (0.18 g, 5.67 mmol) in THF (30 mL) was stirred at 0° C. for 1 h. Then, the mixture was added dropwise to a solution of 2-(4-(2,3-dichlorobenzyl)-3-hydroxy-1H-pyrazol-5-yl)isoindoline-1,3-dione (2 g, 5.15 mmol) in THF (500 mL) and DCM (500 mL), and the mixture was stirred at room temperature for 2 h. It was quenched with water (50 mL), and the solvent was evaporated in vacuo to dryness. The residue was purified by silica gel chromatography eluted with EA:PE=1:1 to give the titled compound (620 mg, 30%) as a white solid. LC/MS: MS (ES+) m/e 402 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.74 (s, 2H), 3.84 (s, 3H), 7.08 (d, J=4.8 Hz, 2H), 7.27-7.31 (m, 1H), 7.94 (s, 5H), 12.27 (s, 1H).

Workup

stirringthe mixture was stirred at room temperature for 2 h
customIt was quenched with water (50 mL)
customthe solvent was evaporated in vacuo to dryness
customThe residue was purified by silica gel chromatography
washeluted with EA

Sources & evidence

ORD record: ord-dc1173133c3247adbd931271ddd2728e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096605B2

Reaction notes

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